


Tallanasty

by Prunes_of_Peace



Category: The Office (US)
Genre: AU, After Hours, Cheating, F/M, Florida, Infidelity, Season 8, Seduction, Smut, Tallahassee - Freeform
Language: English
Status: In-Progress
Published: 2021-02-12
Updated: 2021-02-12
Packaged: 2021-03-12 15:27:24
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,422
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29386989
Author URL: https://archiveofourown.org/users/Prunes_of_Peace/pseuds/Prunes_of_Peace
Summary: Will Jim be able to resist the temptation of Cathy? Set during Season 8, Episode 16 "After Hours." Deleted Scenes do not exist. AU.
Relationships: Jim Halpert/Cathy Simms, Pam Beesly/Jim Halpert
Comments: 5
Kudos: 17





	1. Chapter 1

_What is happening?_ Jim thought to himself in the bathroom. Right outside of the door, in his hotel room, was Cathy Simms. Jim had tried everything he could think of to not be left alone with her — none of his plans came to fruition. Instead, Cathy had become even more cemented in his room by ordering room service and taking a shower. He really thought he was in the clear when Dwight came hurriedly for the bed bugs; however, upon finding no infestation, he stated that he would be spending the night with Nellie instead and not returning. With no alternatives, Jim exited the bathroom.

Upon leaving the bathroom, he immediately saw Cathy's robe on the ground. Cathy was wearing just her lingerie under the covers. Jim had to admit to himself that she looked 'objectively attractive', but no. He was married.

"Alright," Jim said. "I think it's time for you to leave."

"What?" Cathy pleaded. "Ugh. Jim, I thought you were cool with this. You're cool, right?"

"Cathy. Out now."

Just then, a knock was heard at the door. "Room service!"

"C'mon Jim, you're not gonna kick me out all alone without even letting me eat my food, are you?"

"Fine," Jim said. "We'll have dessert, and then you're out."

Jim took the desserts from the room service attendant, tipped him, and closed the door. Jim got on the bed, keeping his distance from Cathy, and handed her the banana foster.

"See? Is this so bad? You're acting like I have the plague, Jim." Cathy mused.

Jim had to chuckle, and began eating. Together, they made light conversation, and Jim tried to not look over at Cathy too much, as her cleavage was on full display. Sure, it wasn't huge, but compared to what little he was seeing at home from Pam, it was more than enticing. _Pam. What would she be thinking if she saw what was happening now?_ Jim was trying to come back to his senses and remember that he needed to kick Cathy out of his room ASAP. However, during their conversation, the mood began to change subtly. Jim began to relax and was cracking jokes with Cathy who answered with witty remarks of her own. Jim had to admit that the experience was not entirely painful and that he was actually enjoying himself quite well.

  
"Oops!" Cathy said, as ice creamed dripped of her spoon onto her chest. "Jim, could you get me a napkin? I seemed to have spilled."

Jim handed Cathy his dessert and grabbed a tissue off the nightstand. "Here you go."

"Um, Jim, my hands are full. Could you get it for me?"

Jim now realized he had fallen into her trap. With no alternatives, Jim daintily rubbed the tissue on her breasts, trying to get as much off as quickly as possible. Cathy giggled under the touch, causing the ice cream to go further down her cleavage. As Jim chased after it, he could feel himself getting slightly excited. _No! I cannot let this happen!_ Jim hastily finished wiping and took back his dessert, crossing his legs as he did so to keep Cathy from getting any inclination that he had just thoroughly enjoyed the contact.

  
Over the course of their meal, Cathy had scooted closer to Jim. Even though she was still under the covers and he over, Jim was still worried about the intimacy. As they finished their desserts, the telephone on Jim's nightstand rang out.

"I'll get it!" exclaimed Cathy as she got out from under the sheets and started climbing over Jim to grab the phone.

_You will definitely NOT get it_ , Jim thought as he reached the phone first and answered the call.

  
"Hello, this is Jim."

_"Hey baby, it's Pam!"_ The telephone stated.

  
"Oh, hey Beesly! How are you doing?" Jim asked nervously. _Shit. Out of all people, why did it have to be her?_ As Jim answered the phone, Cathy crawled into his lap, straddling his legs.

_"How's Tallahassee?"_

  
"Pretty boring, if I'm being totally honest. I haven't even had a chance to prank Dwight yet." Jim was trying to keep his voice sounding normal, which was becoming harder and harder with every passing moment. That wasn't the only thing getting harder either. Cathy had begun slowly rocking on Jim's crotch, and he could feel himself getting aroused. _No, no, no. Not tonight._ Cathy could feel it as well; she let out a squeal of excitement as she picked up her pace.

_"What was that?"_

  
"Oh that? I'm just watching the TV. An episode of Jersey Shore."

_"Honey, you hate Jersey Shore."_

  
"I know! That just shows you the extent of my boredom."

As Pam laughed through the phone, Cathy smiled seductively at Jim, biting her lower lip. All throughout, she continued her rocking, much to Jim's mixed reactions — his mind wanted her to stop, but his body wanted her to go faster. As Jim and Pam continued their conversation, Cathy began running her hands down Jim's chest. This spurred on Jim's growth.

"Hey Pam, listen, I've had a long day, and I've got a busy day tomorrow. I'm going to need to get to sleep soon."

_"Oh! I hadn't realized! Well, goodnight Jim, I love you!"_

  
"Goodnight Pam, love you too." Jim hung up the phone.


	2. Chapter 2

"What the hell are you doing?" Jim demanded.

"Oh c'mon Jim, don't act like you aren't enjoying yourself. We've been having a great night, and I do not want it to end."

"Cathy, I'm married, we cannot be doing this!"

"Well you're not doing much to stop me are you? Besides, I think one part of you wants me to never stop." As Cathy said this, she leaned in and gave Jim a hard, lustful kiss. To Jim's own surprise, he returned the passion, wrapping his arms around her back.

"Mr. Halpert! I knew you would come around eventually!" Said Cathy as she pulled back, only to immediately begin making out with Jim even harder.

_Well_ , Jim thought, _there's no turning back now_. Jim began running his hands up and down Cathy's back as his tongue began battling with hers. Cathy moaned into his mouth and began running her fingers under his sweater.

"Time to lose this," she said as they paused momentarily to lift Jim's sweater and shirt over his head. Jim hungrily returned to her, and she put his head between her petite breasts. 

"I know you've been wanting to do this for a long time. I've seen the way you look at me. I'm going to make this a night you will never forget." Cathy guided Jim's hands down to her ass; he reflexively squeezed and mended them in his hands as his face was buried in Cathy's breasts. Jim was in bliss, feeling emotions that had been suppressed since Pam had gotten pregnant again.  
Cathy began sneaking her hands down Jim's chest until she found his belt buckle. She began undoing it and unzipped his jeans, sticking her hand down his pants. She felt his bulge and began running her hand along the length of it.

"Oh fuck Jim, it feels so big. You want me to suck your cock?"

"Y-yes."

"Say it Jim. 'I want you to suck my cock.'"

"Cathy, I want you to suck my cock." With that, Cathy snaked down Jim's body until her head was at his crotch. Cathy removed Jim's pants, leaving his bulge straining against his boxers. "Mmmm," she said, running her mouth along his length. She began sucking up and down until his briefs were a sloppy mess. With that, Cathy freed Jim's hard-on; it nearly hit her in the face.

"Oh my God, Jim! I never knew you were packing so much, all for me!" Cathy exclaimed as she stared at Jim's dick. She began slowly jerking his cock, much to his delight. "Fuuck," Jim moaned at the feeling. Cathy laughed and began licking up and down his shaft. She moved ever so slowly, feeling every inch and vein.

After getting his dick nicely coated. Cathy enveloped Jim's head in her mouth. She began taking him in, inch by inch, until she was halfway down. Jim could not believe what he was feeling. Sure, Pam had sucked him off a couple times before, but nothing like this. There was no passion behind Pam's motions, only a stale effort to hopefully make Jim satisfied. Cathy, on the other hand, was acting with pure lust. She began bobbing up and down on Jim's shaft, jerking whatever she couldn't fit in her mouth with her hand.

"Fuck Cathy. Don't stop."

"Oh, you think this is something? Just wait." Cathy said. She grabbed onto Jim's thighs for balance and began going down, all the way down, on Jim. She pushed inch after inch into her mouth until all of it was gone. Cathy held Jim there as he squirmed underneath her. After 10 seconds she let go, gasping for air. _Holy Shit. That felt amazing._ Jim grabbed Cathy's head and began pushing her down on his dick, face fucking her. Cathy began moaning and humming, causing Jim to push even faster.

"God, keep suck that dick" Cathy moaned in affirmation and Jim continued to face fuck her. As he felt himself getting close, he slowed down. _No way am I letting the night end this fast._

"Fuck Jim, your dick is so big. I know you like me sucking your cock. I bet Pam never lets you do that." Cathy said, trying to catch her breath.

"You would be correct."

Cathy sat up and began slowly removing her bra, unclasping it, and covering her tits after she removed it. She removed her hand, letting Jim take in her tits in full. Jim sat in awe. _Not as big as Pam's, that's for sure, but they definitely aren't as saggy either._ Cathy turned around, wiggling out of her panties at an excruciatingly slow rate. After tossing them aside, she turned around, showing Jim her freshly shaved pussy, already wet. She straddled his legs, positioning herself over his erect tower. "Now, Jim. Do you want to fuck me?"

"Fuck yeah." With that Cathy slowly lowered herself onto Jim. _God is she tight._ Cathy let out a loud moan as she fully enveloped Jim's massive cock; she began slowly bouncing up and down on his manhood. She began picking up the pace and brought Jim's hands to her breasts. "Oh Fuck, oh fuck, oh fuck," Cathy kept repeating with every slam. "Keep fucking my pussy Jim."

"Keep bouncing baby! Fuuuck Cathy," Jim moaned in pure bliss. So many lustful desires were being released for both of them. Jim was letting out months of celibacy while Cathy was becoming wetter every second knowing that she was finally fucking the man she had wanted since the first day she saw him.

"You like this tight pussy Jim? Is it tighter than your wife's?"

"Oh fuck Cathy, you're so tight."

"Tell me I'm better than Pam. I'm so close Jim. Tell me and I'll go over." Cathy began rubbing her clit at a breakneck speed.

"You're so much tighter than Pam. Fuck Cathy!" Jim felt Cathy begin to convulse around his dick as she went into an orgasm. Cathy moaned so loud, Jim was sure people in the hall could hear, should there be any. _Fuck it, I don't care at this point._

As Cathy rode out her orgasm, Jim began switching positions. He got on top of her, pinning her legs on his shoulders. As Jim began pistoning into her, he leaned forward kissing her hard. Cathy moaned at the rush of the experience. Jim continued pounding into Cathy, folding her in half. "Fuck baby."

"God, Jiiiim! Don't stop don't stop! You're dick is so big! Keeping fucking me!" Jim continued the onslaught, their bodies slapping together. "Fuck Cathy, I'm not done yet. You want this big dick to split you in half?"

"Yes Jim, give it to me!"

"Flip over baby and let me fill you up." Cathy got on her hands and knees, and Jim positioned himself behind her for doggy style. Jim slowly began pushing himself into Cathy's pussy, admiring her ass. Cathy began bucking backwards out of pure want. Jim moved in until he bottomed out, causing Cathy to let out a very sensual moan. And then he began to fuck her. To really fuck her.

Jim began slamming into Cathy's backside, causing a loud clap with every contact. He bottomed out with every stroke, rearranging Cathy's guts. Cathy tried to talk dirty, but all that came out were high-pitched moans. Jim began spanking Cathy in rhythm with his thrusts, causing her snatch to constrict his dick. _God, why have I not been hitting this before?_

"Oh fuck Jim, pound my pussy!" Cathy began rocking back into Jim, meeting his thrusts in sync. _Fuck._ Jim was close. He kept slamming into Cathy, taking handfuls of her petite ass as he did so.

"Cathy, where do you want it?"

"On my face Jim!"

Jim pulled out of Cathy and stood up on the bed. Cathy got on her knees and began jerking his dick at breakneck speed.

"C'mon Jim, I want you to cum for me. Cum all over my face. God I want it sooo bad."

"FUUUUUUUUUUUUCK!"As Cathy edged him on, Jim exploded all over her, coating her face in stream after stream of his hot load. Cathy took it all, continuing to jerk his dick. After the end of his onslaught, she put him back his mouth, eliciting a desperate moan from Jim.

"Fuck Cathy," Jim said as they collapsed together on the bed.

"I know you wanted me, Jim. I'll give you things your wife could never do. I'll fuck you like that any time you want or any time I want. This is just the beginning."

"So that's the Tallanasty?"

Cathy laughed at Jim's quip and rested her head against his chest

As Jim laid there in exhaustion, he thought over what just happened. _I really just cheated on my wife. What have I done?! I said things in bed I have never said before. But it felt so good. I haven't felt that elation in years. Besides, this is Florida. Pam will never find out. I can have a little fun every now and again, right? I still love her, I just need my needs met. Speaking of needs, I can already feel my dick getting hard again. Tallahassee isn't so bad after all."_


End file.
